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Ligand 1,7-dimethylxanthine

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 1,7-dimethylxanthine

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.178

paraxanthine + O2 + NAD(P)H + H+ = 7-methylxanthine + NAD(P)+ + H2O + formaldehyde

722538

-

2.1.1.159

S-adenosyl-L-methionine + 1,7-dimethylxanthine = S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine

670507

-

2.1.1.159

S-adenosyl-L-methionine + paraxanthine = S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine

670568, 670578

-

2.1.1.159

2 entries

2.1.1.160

S-adenosyl-L-methionine + 1,7-dimethylxanthine = S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine

721124, 670276

-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.128

1,3,7-trimethylxanthine + O2 + NADPH + H+ = 1,7-dimethylxanthine + formaldehyde + NADP+ + H2O

-

-

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.128

1,7-dimethylxanthine + 2 O2 + 2 NADH + 2 H+ = xanthine + 2 NAD+ + 2 H2O + 2 formaldehyde

709854

-

1.14.13.128

1,7-dimethylxanthine + 2 O2 + 2 NADPH + 2 H+ = xanthine + 2 NADP+ + 2 H2O + 2 formaldehyde

709854

-

1.14.13.128

1,7-dimethylxanthine + O2 + NADH + H+ = 7-methylxanthine + NAD+ + H2O + formaldehyde

709854

-

1.14.13.128

1,7-dimethylxanthine + O2 + NADPH + H+ = 7-methylxanthine + NADP+ + H2O + formaldehyde

709854

-

1.14.13.178

paraxanthine + O2 + NAD(P)H + H+ = 7-methylxanthine + NAD(P)+ + H2O + formaldehyde

709854, 722538

-

1.14.13.178

paraxanthine + O2 + NADH + H+ = 7-methylxanthine + NAD+ + H2O + formaldehyde

722538

-

1.14.13.128

4 entries

1.14.13.178

2 entries

1.17.3.2

1,7-dimethylxanthine + H2O + O2 = 1,7-dimethylurate + H2o2

659642

-

2.1.1.159

S-adenosyl-L-methionine + 1,7-dimethylxanthine = S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine

670507

-

2.1.1.159

S-adenosyl-L-methionine + paraxanthine = S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine

668585, 670568, 670578, 670577, 670371, 669194

-

2.1.1.159

2 entries

2.1.1.160

S-adenosyl-L-methionine + 1,7-dimethylxanthine = S-adenosyl-L-homocysteine + 1,3,7-trimethylxanthine

721124, 670578, 670276, 690040

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.128

1,3,7-trimethylxanthine + O2 + NADPH + H+ = 1,7-dimethylxanthine + formaldehyde + NADP+ + H2O

-

-

1.14.13.128

caffeine + O2 + NADH + H+ = 1,7-dimethylxanthine + NAD+ + H2O + formaldehyde

-

-

1.14.13.128

2 entries

1.14.13.179

caffeine + O2 + NADH + H+ = paraxanthine + NAD+ + H2O + formaldehyde

-

-

Activator in Enzyme-catalyzed Reactions (2 results)

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Show Activating Compound (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.159

i.e. 1,7-dimethylxanthine, slight stimulation

670507

-

2.1.1.160

i.e. 1,7-dimethylxanthine, slight stimulation

670507

-

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.18

about 9% inhibition at 0.01 mM

759335

-

6.3.4.2

pH-dependent inhibition, overview

702613

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.13.128

0.27

-

pH 7.5, 30°C, kinetic parameters for two-subunit N-demethylase component (Ndm), in the presence of saturating amounts of Ccr (reductase component with cytochrome c reductase activity) and 50 mM Fe2+

709854

1.14.13.178

2.17

-

pH 7.5, 30°C

722538

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.128

0.0504

-

pH 7.5, 30°C, kinetic parameters for two-subunit N-demethylase component (Ndm), in the presence of saturating amounts of Ccr (reductase component with cytochrome c reductase activity) and 50 mM Fe2+

709854

1.14.13.178

0.053

-

pH 7.5, 30°C

722538

2.1.1.159

0.031

-

pH 8.5, 37°C, recombinant CCS1

668585

2.1.1.159

0.07

-

pH 8.5, 30°C

670507

2.1.1.159

0.458

-

recombinant MXMT1

670578

2.1.1.159

0.738

-

recombinant MXMT2

670578

2.1.1.159

4 entries

2.1.1.160

0.973

-

recombinant DXMT1

670578

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

6.3.4.2

0.44

-

pH 8.0, Gln-dependent CTP formation

702613

6.3.4.2

0.48

-

pH 8.0, NH3-dependent CTP formation

702613

6.3.4.2

2 entries

References & Links

Literature References (15)

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Show Reference (15 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

659642

15134930

Studies on the mechanism of action of xanthine oxidase

2004

Choi, E.Y.; Stockert, A.L.; Leimkuhler, S.; Hille, R.

J. Inorg. Biochem.

98

841-848

668585

12527364

Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.)

2003

Mizuno, K.; Okuda, A.; Kato, M.; Yoneyama, N.; Tanaka, H.; Ashihara, H.; Fujimura, T.

FEBS Lett.

534

75-81

669194

11108716

7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties

2001

Ogawa, M.; Herai, Y.; Koizumi, N.; Kusano, T.; Sano, H.

J. Biol. Chem.

276

8213-8218

670276

16333668

Substrate specificity of N-methyltransferase involved in purine alkaloids synthesis is dependent upon one amino acid residue of the enzyme

2006

Yoneyama, N.; Morimoto, H.; Ye, C.X.; Ashihara, H.; Mizuno, K.; Kato, M.

Mol. Genet. Genomics

275

125-135

670371

10984041

Caffeine synthase gene from tea leaves

2000

Kato, M.; Mizuno, K.; Crozier, A.; Fujimura, T.; Ashihara, H.

Nature

406

956-957

670507

-

N-methyltransferases and 7-methyl-N9-nucleoside hydrolase activity in Coffea arabica and the biosynthesis of caffeine

1979

Roberts, M.F.; Waller, G.R.

Phytochemistry

18

451-455

670568

16247553

Caffeine production in tobacco plants by simultaneous expression of three coffee N-methyltranferases and its potential as a pest repellant

2005

Uefuji, H.; Tatsumi, Y.; Morimoto, M.; Kaothien-Nakayama, P.; Ogita, S.; Sano, H.

Plant Mol. Biol.

59

221-227

670577

10364410

Purification and characterization of caffeine synthase from tea leaves

1999

Kato, M.; Mizuno, K.; Fujimura, T.; Iwama, M.; Irie, M.; Crozier, A.; Ashihara, H.

Plant Physiol.

120

579-586

670578

12746542

Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants

2003

Uefuji, H.; Ogita, S.; Yamaguchi, Y.; Koizumi, N.; Sano, H.

Plant Physiol.

132

372-380

690040

-

Expression and location of caffeine synthase in tea plants

2007

Li, Y.; Gu, W.; Ye, S.

Russ. J. Plant Physiol.

54

698-701

702613

20004571

Inhibition of CTP synthase from Escherichia coli by xanthines and uric acids

2010

Roy, A.C.; Lunn, F.A.; Bearne, S.L.

Bioorg. Med. Chem. Lett.

20

141-144

709854

20966097

Characterization of a broad-specificity non-haem iron N-demethylase from Pseudomonas putida CBB5 capable of utilizing several purine alkaloids as sole carbon and nitrogen source

2011

Summers, R.M.; Louie, T.M.; Yu, C.L.; Subramanian, M.

Microbiology

157

583-592

721124

20469646

Essential region for 3-N methylation in N-methyltransferases involved in caffeine biosynthesis

2010

Mizuno, K.; Kurosawa, S.; Yoshizawa, Y.; Kato, M.

Z. Naturforsch. C

65c

257-265

722538

22328667

Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids

2012

Summers, R.M.; Louie, T.M.; Yu, C.L.; Gakhar, L.; Louie, K.C.; Subramanian, M.

J. Bacteriol.

194

2041-2049

759335

29578047

Characterization of a Drosophila glutathione transferase involved in isothiocyanate detoxification

2018

Gonzalez, D.; Fraichard, S.; Grassein, P.; Delarue, P.; Senet, P.; Nicolai, A.; Chavanne, E.; Mucher, E.; Artur, Y.; Ferveur, J.F.; Heydel, J.M.; Briand, L.; Neiers, F.

Insect Biochem. Mol. Biol.

95

33-43

Links to other databases for 1,7-dimethylxanthine

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Show Links (1 entry)

ChEBI

PubChem